Adenosine-5'-triphosphate

Base Information

• Chemical Name: Adenosine-5'-triphosphate
• CAS No.: 56-65-5
• Deprecated CAS: 10168-83-9,16488-07-6,51569-41-6,71800-44-7,84412-18-0,896506-78-8,1259312-93-0,917074-14-7,1259312-93-0,51569-41-6,71800-44-7,84412-18-0,896506-78-8,917074-14-7
• Molecular Formula: C10H16N5O13P3
• Molecular Weight: 507.184
• Hs Code.: HOSPHATE DISODIUM SALT, HYDRATE PRODUCT IDENTIFICATION
• European Community (EC) Number: 200-283-2,631-255-1,686-884-4
• UNII: 8L70Q75FXE
• DSSTox Substance ID: DTXSID6022559
• Nikkaji Number: J10.680A
• Wikipedia: Adenosine_triphosphate
• Wikidata: Q80863
• NCI Thesaurus Code: C209
• Pharos Ligand ID: 13MPPKL52AL3
• Metabolomics Workbench ID: 37298
• ChEMBL ID: CHEMBL14249
• Mol file: 56-65-5.mol

Synonyms:Adenosine Triphosphate;Adenosine Triphosphate, Calcium Salt;Adenosine Triphosphate, Chromium Ammonium Salt;Adenosine Triphosphate, Chromium Salt;Adenosine Triphosphate, Magnesium Chloride;Adenosine Triphosphate, Magnesium Salt;Adenosine Triphosphate, Manganese Salt;Adenylpyrophosphate;ATP;ATP MgCl2;ATP-MgCl2;Atriphos;CaATP;Chromium Adenosine Triphosphate;Cr(H2O)4 ATP;CrATP;Magnesium Adenosine Triphosphate;Manganese Adenosine Triphosphate;MgATP;MnATP;Striadyne

Chemical Property of Adenosine-5'-triphosphate

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 187 - 190oC (Decomposes)
• Boiling Point: 951.429 °C at 760 mmHg
• PKA: pK2: 4.00(-1);pK3: 6.48(-2) (25°C)
• Flash Point: 529.205 °C
• PSA: 308.56000
• Density: 2.636 g/cm³
• LogP: -1.04780
• Storage Temp.: −20°C
• XLogP3: -5.7
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 8
• Exact Mass: 506.99574658
• Heavy Atom Count: 31
• Complexity: 800

Purity/Quality:

99% ^*data from raw suppliers

Adenosine Triphosphate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)O)N
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)O)N
• Recent ClinicalTrials: Functional Magnetic Resonance Imaging of ATP Cough in Chronic Cough Patients
• Recent EU Clinical Trials: Evaluating the effectiveness of the use of intravenous infusions of adenosine triphosphate (ATP) in patients with moderate Alzheimer's Disease and severe: Double-blind dose finding clinical trial.
• Recent NIPH Clinical Trials: The Multicenter Prospective Randomized Controlled Trial Evaluating Efficacy of Pharmacological Approaches to Improve Long-Term Outcome of Catheter Ablation for Atrial Fibrillation: Kansai Plus Atrial Fibrillation (KPAF) trial
• General Description: Adenosine triphosphate (ATP) is a critical molecule in cellular energy metabolism, serving as the primary energy carrier in cells. It plays a key role in signal transduction, particularly in processes such as NLRP3 inflammasome activation, where extracellular ATP can trigger inflammatory responses. Additionally, ATP interacts with polyamines like spermine (SPM), influencing their conformational states and binding affinities, which are essential for cellular functions such as nucleic acid stabilization and enzyme regulation. These interactions highlight ATP's versatility beyond energy transfer, including its involvement in structural and signaling pathways.

Technology Process of Adenosine-5'-triphosphate

There total 64 articles about Adenosine-5'-triphosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

adenosine 5'-diphosphate (58-64-0,905904-58-7) → adenosine-5'-O-(3-thiotriphosphate) (35094-46-3) + ATP (56-65-5,896506-78-8)

Guidance literature:

With dihydroxyacetone phosphate; ethylenediaminetetraacetic acid; DL-dithiothreitol; NAD; trisodium thiophosphate; 2-oxo-propionic acid; magnesium chloride; phosphoglycerate kinase; immobil. triosephosphate isomerase; glyceraldehyde-3-phosphate dehydrogenase; lactate dehydrogenase; In water; for 72h; Ambient temperature; 1) pH 7.5;

DOI:10.1021/jo00182a009

Reference yield: 72.0%

5'-tosyladenosine (5135-30-8) → ATP (56-65-5,896506-78-8)

Guidance literature:

With tetrakis(tetra-n-butylammonium) hydrogen triphosphate; In acetonitrile; for 48h; Ambient temperature;

DOI:10.1016/S0040-4039(01)90180-7

Reference yield: 65.0%

adenosine 5'-<α-thio>triphosphate (29220-54-0) → ATP (56-65-5,896506-78-8)

Guidance literature:

With dihydrogen peroxide;

DOI:10.1021/ol050617r

upstream raw materials:

fructose-1,6-bisphosphate

5'-adenosine monophosphate

Phosphocreatine

adenosine

Downstream raw materials:

UDP

UTP

adenosine 5'-diphosphate

dATP

Refernces

Discovery of Second-Generation NLRP3 Inflammasome Inhibitors: Design, Synthesis, and Biological Characterization

10.1021/acs.jmedchem.9b01155

The research focuses on the discovery and characterization of second-generation NLRP3 inflammasome inhibitors, which are potential drug candidates for neurodegenerative disorders. The study involves the design and synthesis of a new chemical scaffold, HL16, and its analogs, followed by extensive biological testing to evaluate their inhibitory potency and selectivity towards the NLRP3 inflammasome. Experiments include in vitro assays with J774A.1 murine macrophage cells and primary mouse peritoneal macrophages to measure IL-1β production, as well as in vivo testing in mice to assess the compounds' effects on cytokine production and their ability to penetrate the blood-brain barrier. ATP (Adenosine Triphosphate) was used to induce NLRP3 inflammasome activation in cells. The research also encompasses pharmacokinetic studies in rats to determine the systemic clearance, tissue distribution, and oral bioavailability of the lead compound, 17 (YQ128). The analyses used include enzyme-linked immunosorbent assay (ELISA) for cytokine levels, high-performance liquid chromatography (HPLC) for chemical synthesis monitoring, and liquid chromatography tandem mass spectrometry (LC-MS/MS) for plasma and brain tissue concentration measurements of the compounds.

Conformations of spermine in adenosine triphosphate complex: The structural basis for weak bimolecular interactions of major cellular electrolytes

10.1002/chem.201002759

The research focuses on the conformational changes of spermine (SPM), a polyamine that plays a crucial role in various biological processes, when it interacts with adenosine triphosphate (ATP) and ATP–Mg2+ complexes. The study aims to understand the structural basis of the weak interactions between SPM and ATP, which are essential for cellular signal transduction and other biological functions. To achieve this, the researchers synthesized selectively 2H- and 13C-labeled SPMs and analyzed them using NMR spectroscopy to determine the spin–spin coupling constants for six conformationally relevant bonds. The experiments involved the preparation of labeled SPMs, measurement of stoichiometry and association constants in the SPM–ATP complex, and determination of spin–spin coupling constants under various conditions, including different pH levels and in the presence of ATP, ATP–Mg2+, and tripolyphosphate (TPP). The analyses provided insights into the binding affinity, stoichiometry, and conformational changes of SPM upon interaction with these complexes, revealing a preference of SPM for the adenyl group of ATP and its distinct interaction patterns compared to spermidine (SPD). These findings contribute to the understanding of the structural basis of polyamine biological functions.